Time-dependent density functional theory study on the hydrogen bonding-induced twisted intramolecular charge-transfer excited states of 2-(4′-N,N-dimethylaminophenyl)imidazo[4,5-b]pyridine

Journal of Computational Chemistry

Volumn 31, Issue 10, 2010, Pages 2056-2062

  Yin, Shu Hui ^a   Liu, Yufang ^b   Zhang, Wei ^c   Guo, Ming Xing ^a   Song, Peng ^c  

^a DALIAN MARITIME UNIVERSITY   (China)

^b HENAN NORMAL UNIVERSITY   (China)

^c LIAONING UNIVERSITY   (China)

Author keywords

Excited state; Hydrogen bonding; LE; TDDFT; TICT

Indexed keywords

ABSORPTION AND FLUORESCENCE SPECTRA; FLUORESCENCE PEAK; FLUORESCENCE SPECTRA; HYDROGEN BONDING; HYDROGEN BONDINGS; HYDROGEN-BONDED COMPLEXES; INTERMOLECULAR HYDROGEN BONDS; INTRAMOLECULAR CHARGE TRANSFERS; LOCALLY EXCITED STATE; RED-SHIFTED; TIME DEPENDENT DENSITY FUNCTIONAL THEORY; TWO-COMPONENT;

COMPLEXATION; DENSITY FUNCTIONAL THEORY; ELECTRONIC STATES; EXCITED STATES; FLUORESCENCE; HYDROGEN; METHANOL; ORGANIC SOLVENTS; PYRIDINE;

HYDROGEN BONDS;

EID: 77953431138     PISSN: 01928651     EISSN: 1096987X     Source Type: Journal    
DOI: 10.1002/jcc.21492     Document Type: Article

References (88)

1. Lippert, E.; Lüder, W.; Moll, F.; Nagele, H.; Boos, H.; Prigge, H.; Siebold-Blankenstein, I. Angew Chem 1961, 73, 695.
2. Rettig, W. Angew Chem Int Ed Engl 1986, 25, 971.
3. Tan, W.; Zhang, D.-Q.; Wu, H.; Zhu, D.-B. Tetrahedron Lett 2008, 49, 1631.
4. Dobkowski, J.; Grabowski, Z. R.; Waluk, J.; Kühnle, W.; Rettig, W.; Rullière, C.; Yang, W.; Adamus, J.; Gebicki, J. Chem. Sci 1992, 104, 143.
5. Krishnamoorthy, G.; Dogra, S. K. J Colloid Interface Sci 1999, 213, 53.
6. Krishnamoorthy, G.; Dogra, S. K. J Colloid Interface Sci 2000, 228, 335.
7. Krishnamoorthy, G.; Dogra, S. K. J Phys Chem A 2000, 104, 2542.
8. Krishnamoorthy, G.; Dogra, S. K. Chem Phys Lett 2000, 323, 234.
9. Zhang, C.-H.; Chen, Z.-B.; Jiang, Y.-B. Spectrochim Acta A 2004, 60, 2729.
10. Sivakumar, K.; Stalin, T.; Rajendiran, N. Sectrochim Acta A 2005, 62, 991.
11. Chakraborty, A.; Kar, S.; Guchhait, N. Chem Phys 2006, 320, 75.
12. Dekhtyar, M.; Rettig, W.; Weigel, W. Chem Phys 2008, 344, 237.
13. Stsiapura, V. I.; Maskevich, A. A.; Kuzmitsky, V. A.; Uversky, V. N.; Kuznetsova, I. M.; Turoverov, K. K. J Phys Chem B 2008, 112, 15893.
14. Krishnamoorthy, G.; Dogra, S. K. Spectrachim Acta A 1999, 55, 2647.
15. Shayira, B. H.; Pitchumani, K.; Srinivasan, C. J Photochem Photobiol A 2000, 131, 101.
16. Krishnamoorthy, G.; Dogra, S. K. Chem Phys 1999, 243, 45.
17. Krishnamoorthy, G.; Dogra, S. K. Spectrochimica Acta A 1999, 55, 2647.
18. Dey, J.; Dogra, S. K. J Phys Chem 1994, 98, 3638.
19. Sivakumar, K.; Stalin, T.; Rajendiran, N. Spectrochim Acta A 2005, 62, 991.
20. Huerta, F. F.; Laxmi, Y. R. S.; Buckvall, J. E. Org Lett 2000, 2, 1037.
21. Benali, B.; Kabouchi, B.; Cazeau-Dubroca, C. J Mol Liq 2000, 87, 69.
22. Boren, L.; Martin-Matute, B.; Xu, Y. M.; Cordova, A.; Buckvall, J. E. Chem Eur J 2006, 12, 225.
23. Grabowski, Z. R.; Rotkiewicz, K.; Rettig, W. Chem Rev 2003, 103, 3899.
24. Aleksiejew, M.; Heldt, J.; Heldt, J. R. J Lumin 2009, 129, 208.
25. Mondal, J. A.; Ghosh, H. N.; Ghanty, T. K.; Mukherjee, T.; Palit, D. K. J Phys Chem A 2006, 110, 3432.
26. Maliakal, A.; Lem, G.; Turro, N. J.; Ravichandran, R.; Suhadolnik, J. C.; DeBellis, A. D.; Wood, M. G.; Lau, J. J Phys Chem A 2002, 106, 7680.
27. Zhang, Y.; Xie, T. X.; Han, K. L.; Zhang, J. Z. H. J Chem Phys 2003, 119, 12921.
28. Khalil, O. S.; Meeks, J. S.; McGlynm, S. P. Chem Phys Lett 1989, 162, 165.
29. Kosower, E. M.; Dodiuk, H. J Am Chem Soc 1976, 98, 924.
30. Chandross, A. In Exciplex; Gordon, M.; Ware, M., Eds.; Academic Press: New York, 1975; p. 187.
31. Visser, R. J.; Wiesenborn, P. C. M.; Varma, C. A. G. O. Chem Phys Lett 1985, 113, 330.
32. Rotkeiwicz, K.; Greltmann, K. H.; Grabowski, Z. R. Chem Phys Lett 1973, 19, 315.
33. Chu, T. S.; Zhang, Y.; Han, K. L. Int: Rev Phys Chem 2006, 25, 201.
34. Jödicke, C. J.; Lüthi, P. H. J Am Chem Soc 2003, 125, 252.
35. Jamorski, C. J.; Casida, M. E. J Phys Chem B 2004, 108, 7132.
36. Rappoport, D.; Furche, F. J Am Chem Soc 2004, 126, 1277.
37. Zhang, Y.; Xie, T. X.; Han, K. L. J Phys Chem. A 2003, 107, 10893.
38. Köhn, A.; Hättig, C. J Am Chem Soc 2004, 126, 7399.
39. Yang, J. S.; Liau, K. L.; Wang, C. M.; Hwang, C. Y. J Am Chem Soc 2004, 126, 12325.
40. Kim, Y. H.; Cho, D. W.; Yoon, M.; Kim, D. J Phys Chem 1996, 100, 15670.
41. Hicks, J.; Vandersall, M.; Babarogic, Z.; Eisenthal, K. E. Chem Phys Lett 1985, 116, 18.
42. Levy, A.; Avnir, D.; Ottolenghi, M. Chem Phys Lett 1985, 121, 233.
43. Cazeau-Dubroca, C.; Lyazidi, S. A.; Cambou, P.; Peirigua, A.; Cazeau, Ph.; Pesquer, M. J Phys Chem 1989, 93, 2347.
44. Fasani, E.; Albini, A.; Savarino, P.; Viscardi, G.; Bami, E. J Heterocycl Chem 1993, 30, 1041.
45. Chu, T. S.; Han, K. L. Phys Chem Chem Phys 2008, 10, 2431.
46. Abraham, E.; Oberlé, J.; Jonusauskas, G.; Lapouyade, R.; Rullière, C. Chem Phys 1997, 214, 409.
47. Barik, A.; Kumbhakar, M.; Nath, S.; Pal, H. Chem Phys 2005, 315, 277.
48. Liu, Y.-F.; Ding, J.-.X.; Shi, D.-H.; Sun, J.-F. J Phys Chem A 2008, 112, 6244.
49. Liu, Y.-F.; Ding, J.-X.; Liu, R.-Q.; Shi, D.-H.; Sun, J.-F. J Comput Chem 2009, 30, 2723.
50. Bangal, P. R.; Panja, S.; Chakravorti, S. J Photochem Photobiol A 2001, 139, 5.
51. Singh, S. T.; Mitra, S. J Lumin 2007, 127, 508.
52. Kwok, W. M.; Ma, C.; George, M. W.; Grills, D. C.; Matousek, P.; Parker, A. W.; Phillips, D.; Toner, W. T.; Towrie, M. Photochem Photobiol Sci 2007, 6, 987.
53. Mahanta, S.; Singh, R. B.; Kar, S.; Guchhait, N. J Photochem Photobiol A 2008, 194, 318.
54. Zhao, G.-J.; Han, K.-L. J Phys Chem A 2007, 111, 2469.
55. Zhao, G.-J.; Han, K.-L. J Phys Chem A 2007, 111, 9218.
56. Zhao, G.-J.; Liu, J.-Y.; Zhou, L.-C.; Han, K.-L. J Phys Chem B 2007, 111, 8940.
57. Zhou, L.-C.; Zhao, G.-J.; Liu, J.-F.; Han, K.-L.; Wu, Y.-K.; Peng, X.-J.; Sun, M.-T. J Photochem Photobiol A 2007, 187, 305.
58. Zhou, L.-C.; Liu, J.-F.; Zhao, G.-J.; Shi, Y.; Peng, X.-J.; Han, K.-L. Chem Phys 2007, 333, 179.
59. Wan, S.-B.; Liu, S.-S.; Zhao, G.-J.; Chen, M.-D.; Han, K.-L.; Sun, M.-T. Biophys Chem 2007, 129, 218.
60. Zhao, G.-J.; Han, K.-L. J Chem. Phys 2007, 127, 024306.
61. Zhao, G.-J.; Han, K.-L.; Lei, Y.-B.; Dou, Y.-S. J Chem Phys 2007, 127, 094307.
62. Han, K.-L.; He, G.-Z.; Lou, N.-Q. J Chem Phys 1996, 105, 8699.
63. Han, K.-L.; He, G.-Z. J Photochem Photobiol C 2007, 8, 55.
64. Zhao, G.-J.; Han, K. L. Biophys J 2008, 94, 38.
65. Zhao, G.-J.; Han, K.-L. J Comput Chem 2008, 29, 2010.
66. Chen, R.-K.; Zhao, G.-J.; Yang, X.-C.; Jiang, X.; Liu, J.-F.; Tian, H.-N.; Gao, Y.; Liu, X.; Han, K.-L.; Sun, M.-T.; Sun, L.-C. J Mol Struct 2008, 876, 102.
67. Zhao, G.-J.; Chen, R.-K.; Sun, M.-T.; Liu, J.-Y.; Li, G.-Y.; Gao, Y.-L.; Han, K.-L.; Yang, X.-C.; Sun, L.-C. Chem Eur J 2008, 14, 6935.
68. Zhao, G.-J.; Liu, Y.-H.; Han, K.-L.; Dou, Y. S. Chem Phys Lett 2008, 453, 29.
69. Zhao, G.-J.; Han, K.-L. Chem Phys Chem 2008, 9, 1842.
70. Zhao, G.-J.; Han, K.-L. J Phys Chem A 2009, 113, 4788.
71. Chai, S.; Zhao, G.-J.; Song, P.; Yang, S.-Q.; Liu, J.-Y.; Han, K.-L. Phys Chem. Chem Phys 2009, 11, 4385.
72. Zhao, G.-J.; Han, K.-L. J Phys Chem A 2009, 113, 14329-14335.
73. Zhao, G.-J.; Han, K.-L.; Stang, P. J. J Chem Theory Comput 2009, 5, 1955.
74. Peng, X.-J.; Wu, Y.-K.; Fan, J.-L.; Tian, M.-Z.; Han, K.-L. J Org Chem 2005, 70, 10524.
75. Zhang, H.; Smith, S. C J Theor Comput Chem 2007, 6, 789.
76. Zhang, H.; Wang, S.; Sun, Q.; Smith, S. C. Phys Chem Chem Phys 2009, 11, 8422.
77. Nakajima, S.; Sumimoto, M.; Nakao, Y.; Sato, H.; Sakaki, S.; Osakada, K. Organometallics 2005, 24, 4029.
78. Imabayashi, T.; Fujiwara, Y.; Nakao, Y.; Sato, H.; Sakaki, S. Organometallics 2005, 24, 2129.
79. Ohnishi, Y. Y.; Nakao, Y.; Sato, H.; Sakaki, S. Organometallics 2006, 25, 3352.
80. Saito, K.; Nakao, Y.; Sato, H.; Sakaki, S. J Phys Chem A 2006, 110, 9710.
81. Ray, M.; Nakao, Y.; Sato, H.; Sakaba, H.; Sakaki, S. J Am Chem Soc 2006, 128, 11927.
82. Ray, M.; Nakao, Y.; Sato, H.; Sakaki, S. Organometallics 2006, 26, 4413.
83. Dash, N.; Chipem, F. A. S.; Swaminathan, R.; Krishnamoorthy, G. Chem Phys Lett 2008, 460, 119.
84. Becke, A. D. J Chem Phys 1993, 98, 5648.
85. Schäfer, A.; Huber, C.; Ahlrichs, R. J Chem Phys 1994, 100, 5829.
86. Ahlrichs, R.; Bär, M.; Horn, H.; Kölmel, C Chem Phys Lett 1989, 162, 165.
87. Ray, M.; Nakao, Y.; Sato, H.; Sakaba, H.; Sakaki, S. J Am Chem Soc 2006, 128, 11927.
88. Furche, F.; Ahlrichs, R. J Chem Phys 2002, 117, 7433.